4-(N,N-dimethlyamino)pyridine in acetonitrile T=24°C; 12 h;

1: 48.3 percent / triphenylphosphine, diethyl azodicarboxylate / dioxane / 48 h / 24 °C 2: 93 percent / NaOH / methanol / 48 h / Ambient temperature 3: 47.9 percent / aq. sodium acetate, aq. acetic acid, KI / ethanol; H2O / 30 h / 37 - 40 °C / pH=4.5 4: 89 percent / pyridine / 12 h 5: 50 percent / 4-(dimethylamino)pyridine / acetonitrile / 12 h / 24 °C View Scheme

1: 47.9 percent / aq. sodium acetate, aq. acetic acid, KI / ethanol; H2O / 30 h / 37 - 40 °C / pH=4.5 2: 89 percent / pyridine / 12 h 3: 50 percent / 4-(dimethylamino)pyridine / acetonitrile / 12 h / 24 °C View Scheme

1: 89 percent / pyridine / 12 h 2: 50 percent / 4-(dimethylamino)pyridine / acetonitrile / 12 h / 24 °C View Scheme

1: 48.3 percent / triphenylphosphine, diethyl azodicarboxylate / dioxane / 48 h / 24 °C 2: 93 percent / NaOH / methanol / 48 h / Ambient temperature 3: 47.9 percent / aq. sodium acetate, aq. acetic acid, KI / ethanol; H2O / 30 h / 37 - 40 °C / pH=4.5 4: 89 percent / pyridine / 12 h 5: 50 percent / 4-(dimethylamino)pyridine / acetonitrile / 12 h / 24 °C View Scheme

2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in toluene 3 h; Heating;